4-氨基-1,2,5-恶二唑-3-羧酸甲酯 | 159013-94-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酯类氨基酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 中文名称: 4-氨基-1,2,5-恶二唑-3-羧酸甲酯
• 英文名称: 3-amino-4-carbmethoxyfurazan
• 英文别名: Methyl 4-amino-1,2,5-oxadiazole-3-carboxylate
• CAS: 159013-94-2
• 化学式: C₄H₅N₃O₃
• mdl: MFCD00465007
• 分子量: 143.102
• InChiKey: PNFAQDARRSPFKS-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155 °C(Solv: chloroform (67-66-3))
• 沸点：
  257.6±43.0 °C(Predicted)
• 密度：
  1.447±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氨基-1,2,5-恶二唑-3-羧酸甲酯 在 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以85%的产率得到4-氨基-1,2,5-恶二唑-3-甲酰肼
  参考文献：
  名称：

  2-[(4-aminofurazan-3-yl)-1H-1,2,4-triazol-5-yl] 乙酸衍生物的合成和一些转化

  摘要：

  开发了两种合成在 5 位带有氨基呋喃基取代基的 1,2,4-三唑基乙酸酯的方法。三唑环是通过 3-氨基呋咱甲酸酰肼或脒腙与乙氧基羰基乙基乙酰亚胺盐酸盐的环缩合反应形成的。

  DOI：

  10.1007/s11172-018-2325-y
• 作为产物：
  描述：

  3-氨基呋咱-4-羧酸 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以91%的产率得到4-氨基-1,2,5-恶二唑-3-羧酸甲酯
  参考文献：
  名称：

  Discovery of Selective Small-Molecule Inhibitors for the β-Catenin/T-Cell Factor Protein–Protein Interaction through the Optimization of the Acyl Hydrazone Moiety

  摘要：

  Acyl hydrazone is an important functional group for the discovery of bioactive small molecules. This functional group is also recognized as a pan assay interference structure. In this study, a new small-molecule inhibitor for the beta-catenin/Tcf protein-protein interaction (PPI), ZINC02092166, was identified through AlphaScreen and FP assays. This compound contains an acyl hydrazone group and exhibits higher inhibitory activities in cell-based assays than biochemical assays. Inhibitor optimization resulted in chemically stable derivatives that disrupt the beta-catenin/Tcf PPI. The binding mode of new inhibitors was characterized by site-directed mutagenesis and structure-activity relationship studies. This series of inhibitors with a new scaffold exhibits dual selectivity for beta-catenin/Tcf over beta-catenin/cadherin and beta-catenin/APC PPIs. One derivative of this series suppresses canonical Wnt signaling, downregulates the expression of Wnt target genes, and inhibits the growth of cancer cells. This compound represents a solid starting point for the development of potent and selective beta-catenin/Tcf inhibitors.

  DOI：

  10.1021/acs.jmedchem.5b00223

文献信息

• IDO1 INHIBITOR AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：SHANDONG LUYE PHARMACEUTICAL CO., LTD.

  公开号：US20190169140A1

  公开（公告）日：2019-06-06

  A compound as an indoleamine-2,3-dioxygenase 1 (IDO1) inhibitor, and an application thereof in the field of IDO1-related diseases, and in particular a compound as shown in formula (I) and a pharmaceutically acceptable salts thereof.

  一种作为吲哌酮胺-2,3-二氧化酶1（IDO1）抑制剂的化合物，以及其在IDO1相关疾病领域中的应用，特别是如公式（I）所示的化合物及其药用可接受的盐。
• [EN] METHODS AND COMPOSITIONS OF SUBSTITUTED 5H-[1,2,5]OXADIAZOLO[3',4':5,6] PYRAZIONO[2,3-B]INDOLE ANALOGS AS INHIBITORS OF BETA-CATENIN/T-CELL FACTOR PROTEIN-PROTEIN INTERACTIONS<br/>[FR] PROCÉDÉS ET COMPOSITIONS D'ANALOGUES SUBSTITUÉS DE 5H-[1,2,5]OXADIAZOLO[3',4':5,6] PYRAZIONO[2,3-B]INDOLE UTILISÉS COMME INHIBITEURS DES INTERACTIONS PROTÉINE-PROTÉINE BÊTA-CATÉNINE/FACTEURS TCF
  申请人：UNIV UTAH RES FOUND

  公开号：WO2016187050A1

  公开（公告）日：2016-11-24

  In one aspect, the invention relates to substituted 5H-[1,2,5]oxadiazolo [3',4':5,6]pyrazino[2,3-b]indole analogues, derivatives thereof, and related compound; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating disorders, e.g., various tumors and cancers, associated with a β-catenin/T-cell factor interaction dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  在一个方面，该发明涉及替代的5H-[1,2,5]噁二唑[3',4':5,6]吡唑并[2,3-b]吲哚类似物，其衍生物以及相关化合物；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与β-连环蛋白/T细胞因子相互作用功能障碍相关的疾病的方法，例如各种肿瘤和癌症。本摘要旨在作为在特定领域搜索的扫描工具，并不旨在限制本发明。
• A Facile and Versatile Synthesis of Energetic Furazan‐Functionalized 5‐Nitroimino‐1,2,4‐Triazoles
  作者：Zhen Xu、Guangbin Cheng、Hongwei Yang、Xuehai Ju、Ping Yin、Jiaheng Zhang、Jean'ne M. Shreeve

  DOI：10.1002/anie.201701659

  日期：2017.5.15

  An analogue‐oriented synthetic route for the formulation of furazan‐functionalized 5‐nitroimino‐1,2,4‐triazoles has been explored. The process was found to be straightforward, high yielding, and highly efficient, and scalable. Nine compounds were synthesized and the physicochemical and energetic properties, including density, thermal stability, and sensitivity, were investigated, as well as the energetic

  探索了以类似物为导向的合成路线，用于制备呋喃山官能化的5-硝基亚氨基-1,2,4-三唑。发现该过程是直接的，高产量的，高效的和可扩展的。合成了9种化合物，并使用EXPLO5代码研究了包括密度，热稳定性和敏感性在内的物理化学和能量特性，以及能量性能（例如，爆轰速度和爆轰压力）。在这些新的材料，化合物4 - 6和11具有高密度，可接受的敏感性和良好的爆轰性能，并由此证明了潜在的应用作为新的辅助炸药。
• 1,3,4‐Oxadiazole Bridges: A Strategy to Improve Energetics at the Molecular Level
  作者：Jinchao Ma、Ajay Kumar Chinnam、Guangbin Cheng、Hongwei Yang、Jiaheng Zhang、Jean'ne M. Shreeve

  DOI：10.1002/anie.202014207

  日期：2021.3

  analyses. The thermal stability, friction sensitivity, impact sensitivity, detonation velocity, and detonation pressure were evaluated. The hydroxylammonium salt 8 has an excellent detonation performance (D=9101 m s−1, P=37.9 GPa) and insensitive properties (IS=17.4 J, FS=330 N), which show its great potential as a high‐performance insensitive explosive. Using quantum computation and crystal structure analysis

  由于低的热和/或机械稳定性，迄今为止合成的许多高能材料具有有限的应用。可以通过引入结构修饰（例如桥接基团）来克服此限制。在本研究中，制备了一系列1,3,4-恶二唑桥连的呋喃唑。通过1 H和13 C NMR，红外，元素和X射线晶体学分析确认了它们的结构。评价了热稳定性，摩擦敏感性，冲击敏感性，爆炸速度和爆炸压力。羟铵盐8具有优异的爆震性能（D＝ 9101m s -1，P= 37.9 GPa）和不敏感的特性（IS = 17.4 J，FS = 330 N），显示出其作为高性能不敏感炸药的巨大潜力。使用量子计算和晶体结构分析，引入1,3,4-恶二唑部分对分子反应性以及单和双1,3,4-恶二唑桥的敏感性和热稳定性之间的差异是经过考虑的。引入1,3,4-恶二唑的合成方法以及对1,3,4-恶二唑桥联化合物的系统研究为未来的高能学设计提供了理论依据。
• Synthesis and x-ray study of novel azofurazan-annulated macrocyclic lactams
  作者：Aleksei B. Sheremetev、Nataliya S. Aleksandrova、Dmitrii E. Dmitriev、Boris B. Averkiev、Mikhail Yu. Antipin

  DOI：10.1002/jhet.5570420408

  日期：2005.5

  Reaction of 1,4-di-(3-aminofurazan-4-oyl)piperazine 4 with dibromoisocyanurate (DBI) affords azofurazan-annulated macrocyclic lactam 7; the X-ray structure of the macrocycle 7 is reported. The synthesis was started with 3-aminofurazan-4-carboxylic acid 1. A one-pot method for preparation of the amino acid was elaborated from commercially available cyanoacetic ester. Amides of the acid have been prepared

  1，4-二-（3-氨基呋喃-4-甲酰基）哌嗪4与二溴异氰脲酸酯（DBI）的反应得到氮杂呋喃-环化的大环内酰胺7；报告了大环7的X射线结构。用3-氨基呋喃-4-羧酸1开始合成。从市场上可买到的氰基乙酸酯阐述了一种制备氨基酸的一锅法。酸的酰胺是通过酯化和随后的动画制备的。